Experimental strategies for increasing the catalyst turnover number in a continuous Heck coupling reaction

Ludmila Peeva; João da Silva Burgal; Shankul Vartak; Andrew G. Livingston

doi:10.1016/j.jcat.2013.06.020

Experimental strategies for increasing the catalyst turnover number in a continuous Heck coupling reaction

Ludmila Peeva
, João da Silva Burgal
, Shankul Vartak
, Andrew G. Livingston^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

54 Citations (Scopus)

Abstract

This work presents a continuous Heck coupling reaction combined with organic solvent nanofiltration (OSN) separation of the catalyst in situ, using polymeric membranes at high temperature (80 C) and high concentration of base (>0.9 mol L-1). Two reactor configurations are investigated: a continuous single stirred tank reactor/membrane separator (m-CSTR) and a plug flow reactor (PFR) followed by m-CSTR (PFR-m-CSTR). The combined PFR-m-CSTR configuration was found to be the most promising, achieving conversions above 98% and high catalyst turnover numbers (TONs) of ∼20,000. In addition, low contamination of the product stream (∼27 mg Pd per kg of product) makes this process configuration attractive for the pharmaceutical industry.

Original language	English
Pages (from-to)	190-201
Number of pages	12
Journal	Journal of Catalysis
Volume	306
DOIs	https://doi.org/10.1016/j.jcat.2013.06.020
Publication status	Published - 2013
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

Keywords

Continuous heck coupling reaction
High catalyst TON
Low contamination of the product stream
Organic solvent nanofiltration (OSN)
Pd retention in situ
PEEK membrane

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10.1016/j.jcat.2013.06.020

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title = "Experimental strategies for increasing the catalyst turnover number in a continuous Heck coupling reaction",

abstract = "This work presents a continuous Heck coupling reaction combined with organic solvent nanofiltration (OSN) separation of the catalyst in situ, using polymeric membranes at high temperature (80 C) and high concentration of base (>0.9 mol L-1). Two reactor configurations are investigated: a continuous single stirred tank reactor/membrane separator (m-CSTR) and a plug flow reactor (PFR) followed by m-CSTR (PFR-m-CSTR). The combined PFR-m-CSTR configuration was found to be the most promising, achieving conversions above 98\% and high catalyst turnover numbers (TONs) of ∼20,000. In addition, low contamination of the product stream (∼27 mg Pd per kg of product) makes this process configuration attractive for the pharmaceutical industry.",

keywords = "Continuous heck coupling reaction, High catalyst TON, Low contamination of the product stream, Organic solvent nanofiltration (OSN), Pd retention in situ, PEEK membrane",

author = "Ludmila Peeva and Burgal, \{Jo{\~a}o da Silva\} and Shankul Vartak and Livingston, \{Andrew G.\}",

note = "Funding Information: This work was funded by the Novartis Pharma AG, Massachusetts Institute of Technology subaward Agreement No. 5710002924 ; The authors would like to acknowledge also the financial support from the U.K. Engineering and Physical Sciences Research Council (EPSRC) Grant No. EP/G070172/1 – ELSEP and the EC FP7 Ares(2011)1042335 – MEMTIDE . Copyright: Copyright 2013 Elsevier B.V., All rights reserved.",

year = "2013",

doi = "10.1016/j.jcat.2013.06.020",

language = "English",

volume = "306",

pages = "190--201",

journal = "Journal of Catalysis",

issn = "0021-9517",

publisher = "Academic Press Inc.",

}

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AU - Peeva, Ludmila

AU - Burgal, João da Silva

AU - Vartak, Shankul

AU - Livingston, Andrew G.

N1 - Funding Information: This work was funded by the Novartis Pharma AG, Massachusetts Institute of Technology subaward Agreement No. 5710002924 ; The authors would like to acknowledge also the financial support from the U.K. Engineering and Physical Sciences Research Council (EPSRC) Grant No. EP/G070172/1 – ELSEP and the EC FP7 Ares(2011)1042335 – MEMTIDE . Copyright: Copyright 2013 Elsevier B.V., All rights reserved.

PY - 2013

Y1 - 2013

N2 - This work presents a continuous Heck coupling reaction combined with organic solvent nanofiltration (OSN) separation of the catalyst in situ, using polymeric membranes at high temperature (80 C) and high concentration of base (>0.9 mol L-1). Two reactor configurations are investigated: a continuous single stirred tank reactor/membrane separator (m-CSTR) and a plug flow reactor (PFR) followed by m-CSTR (PFR-m-CSTR). The combined PFR-m-CSTR configuration was found to be the most promising, achieving conversions above 98% and high catalyst turnover numbers (TONs) of ∼20,000. In addition, low contamination of the product stream (∼27 mg Pd per kg of product) makes this process configuration attractive for the pharmaceutical industry.

AB - This work presents a continuous Heck coupling reaction combined with organic solvent nanofiltration (OSN) separation of the catalyst in situ, using polymeric membranes at high temperature (80 C) and high concentration of base (>0.9 mol L-1). Two reactor configurations are investigated: a continuous single stirred tank reactor/membrane separator (m-CSTR) and a plug flow reactor (PFR) followed by m-CSTR (PFR-m-CSTR). The combined PFR-m-CSTR configuration was found to be the most promising, achieving conversions above 98% and high catalyst turnover numbers (TONs) of ∼20,000. In addition, low contamination of the product stream (∼27 mg Pd per kg of product) makes this process configuration attractive for the pharmaceutical industry.

KW - Continuous heck coupling reaction

KW - High catalyst TON

KW - Low contamination of the product stream

KW - Organic solvent nanofiltration (OSN)

KW - Pd retention in situ

KW - PEEK membrane

UR - https://www.scopus.com/pages/publications/84881160909

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DO - 10.1016/j.jcat.2013.06.020

M3 - Article

AN - SCOPUS:84881160909

SN - 0021-9517

VL - 306

SP - 190

EP - 201

JO - Journal of Catalysis

JF - Journal of Catalysis

ER -

Experimental strategies for increasing the catalyst turnover number in a continuous Heck coupling reaction

Abstract

UN SDGs

Keywords

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